Direct photopatterning of robust and diverse materials
Abstract
The present invention relates to methods of metathesizing olefins using catalysts previously considered to be practically inactive. The present invention further relates to novel photosensitive compositions, their use as photoresists, and methods related to patterning polymer layers on substrates. Further, modifications to the compositions and method provide for an unprecedented functionalization of the compositions, useful for example in the preparation of sensors, drug delivery systems, and tissue scaffolds. The novel compositions and associated methods also provide for the opportunity to prepare 3-dimensional objects which provide new access to critically dimensioned devices, including for example photonic devices.
- Inventors:
- Issue Date:
- Research Org.:
- California Institute of Technology (CalTech), Pasadena, CA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1771490
- Patent Number(s):
- 10799613
- Application Number:
- 14/505,824
- Assignee:
- California Institute of Technology (Pasadena, CA)
- Patent Classifications (CPCs):
-
A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61L - METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL
C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08F - MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- DOE Contract Number:
- SC0001293
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 10/03/2014
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Weitekamp, Raymond, Grubbs, Robert H., Atwater, Harry A., and Fakonas, James. Direct photopatterning of robust and diverse materials. United States: N. p., 2020.
Web.
Weitekamp, Raymond, Grubbs, Robert H., Atwater, Harry A., & Fakonas, James. Direct photopatterning of robust and diverse materials. United States.
Weitekamp, Raymond, Grubbs, Robert H., Atwater, Harry A., and Fakonas, James. Tue .
"Direct photopatterning of robust and diverse materials". United States. https://www.osti.gov/servlets/purl/1771490.
@article{osti_1771490,
title = {Direct photopatterning of robust and diverse materials},
author = {Weitekamp, Raymond and Grubbs, Robert H. and Atwater, Harry A. and Fakonas, James},
abstractNote = {The present invention relates to methods of metathesizing olefins using catalysts previously considered to be practically inactive. The present invention further relates to novel photosensitive compositions, their use as photoresists, and methods related to patterning polymer layers on substrates. Further, modifications to the compositions and method provide for an unprecedented functionalization of the compositions, useful for example in the preparation of sensors, drug delivery systems, and tissue scaffolds. The novel compositions and associated methods also provide for the opportunity to prepare 3-dimensional objects which provide new access to critically dimensioned devices, including for example photonic devices.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2020},
month = {10}
}
Works referenced in this record:
High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes
patent-application, January 2009
- Grubbs, Robert H.; Schwab, Peter; Nguyen, Sonbinh T.
- US Patent Application 11/929212; 20090012254
Method of production of three-dimensional objects by stereolithography
patent, November 1996
- Hull, Charles W.
- US Patent Document 5,571,471
High metathesis activity ruthenium and osmium carbene complexes
patent, July 2010
- Grubbs, Robert H.; Schwab, Peter; Nguyen, SonBinh T.
- US Patent Document 7,750,172
Ruthenium metal alkylidene complexes coordinated with triazolylidene ligands that exhibit high olefin metathesis activity
patent, September 2003
- Grubbs, Robert H.; Trnka, Tina
- US Patent Document 6,624,265
Catalyst Compositions and Their Use for Hydrogenation of Nitrile Rubber
patent-application, May 2015
- Obrecht, Werner; David, Sarah; Liu, Qingchun
- US Patent Application 14/352073; 20150126683
Highly Ordered Dielectric Mirrors via the Self-Assembly of Dendronized Block Copolymers
journal, October 2013
- Piunova, Victoria A.; Miyake, Garret M.; Daeffler, Christopher S.
- Journal of the American Chemical Society, Vol. 135, Issue 41
Precisely Tunable Photonic Crystals From Rapidly Self-Assembling Brush Block Copolymer Blends
journal, September 2012
- Miyake, Garret M.; Piunova, Victoria A.; Weitekamp, Raymond A.
- Angewandte Chemie International Edition, Vol. 51, Issue 45, p. 11246-11248
Manufacture of void-free laminates and use thereof
patent, May 2002
- Xu, Guo-Feng; Repecka, Linas; Mortimer, Steve
- US Patent Document 6,391,436
Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis
patent, January 2010
- Herrmann, Wolfgang Anton; Schattenmann, Wolfgang; Weskamp, Thomas
- US Patent Document 7,652,145
Synthesis of ruthenium or osmium metathesis catalysts
patent, January 2003
- Grubbs, Robert H.; Belderrain, Tomas R.; Brown, Seth N.
- US Patent Document 6,504,041
Ruthenium Olefin Metathesis Catalysts Bearing N-Heterocyclic Carbene Ligands with Substituted Backbone
patent-application, May 2011
- Grubb, Robert H.; Chung, Cheol Keun; Bourg, Jean-Baptiste
- US Patent Application 12/936917; 20110124868
Pattern Forming Method, Resist Composition for Multiple Development Used in the Pattern Forming Method, Developer for Negative Development Used in the Pattern Forming Method, and Rinsing Solution for Negative Development Used in the Pattern Forming Method
patent-application, October 2008
- Tsubaki, Hideaki; Kanna, Shinichi
- US Patent Application 12/145270; 20080261150
Photoinitiated Olefin Methathesis Polymerization
patent-application, April 2014
- Weitekamp, Raymond; Grubbs, Robert H.
- US Patent Application 14/044974; 20140099573
High metathesis activity ruthenium and osmium metal carbene complexes
patent, October 2004
- Grubbs, Robert H.; Schwab, Peter; Nguyen, SonBinh T.
- US Patent Document 6,806,325
Synthesis of ruthenium of osmium metathesis catalysts
patent-application, February 2002
- Grubbs, Robert H.; Belderrain, Tomas R.; Brown, Seth N.
- US Patent Application 09/967198; 20020022733
Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts
patent, July 2004
- Grubbs, Robert H.; Love, Jennifer; Sanford, Melanie S.
- US Patent Document 6,759,537
Synthesis of ruthenium or osmium metathesis catalysts
patent, April 2000
- Grubbs, Robert H.; Belderrain, Tomas R.; Brown, Seth N.
- US Patent Document 6,048,993
Use of Methanofullerne Derivatives as Resist Materials and Method for Forming a Resist Layer
patent-application, May 2008
- Robinson, Alex; Preece, Jon Andrew; Palmer, Richard Edward
- US Patent Application 11/662904; 20080118874
High metathesis activity ruthenium and osmium metal carbene complexes
patent-application, November 2001
- Grubbs, Robert H.; Schwab, Peter; Nguyen, Sonbinh T.
- US Patent Application 09/746146; 20010039360
High activity ruthenium and osmium metal carbene complexes for olefin metathesis reactions
patent, October 1999
- Grubbs, Robert H.; Nguyen, SonBinh T.; Johnson, Lynda Kaye
- US Patent Document 5,969,170
Modified cycloolefin copolymer
patent, December 1999
- Hatke, Wilfried; Osan, Frank; Herrmann-Schonherr, Otto
- US Patent Document 6,008,298
Method for forming patterns for semiconductor devices
patent, July 2004
- Andry, Paul S.; Flake, John C.; Michel, Bruno
- US Patent Document 6,767,828
Sputtering magnetron control devices
patent-application, January 2006
- Hatch, Gareth P.; Ras, Christopher A.
- US Patent Application 11/182596; 20060011470
Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis
patent, May 2008
- Herrmann, Wolfgang Anton; Schattenmann, Wolfgang; Weskamp, Thomas
- US Patent Document 7,378,528
Imidazolidine-based metal carbene metathesis catalysts
patent, February 2008
- Grubbs, Robert H.; Scholl, Matthias
- US Patent Document 7,329,758
Poly(thienylenevinylene) prepared by ring-opening metathesis polymerization: Performance as a donor in bulk heterojunction organic photovoltaic devices
journal, March 2010
- Horie, Masaki; Shen, I. -Wen; Tuladhar, Sachetan M.
- Polymer, Vol. 51, Issue 7
High metathesis activity ruthenium and osmium metal carbene complexes
patent, October 2007
- Grubbs, Robert H.; Schwab, Peter; Nguyen, SonBinh T.
- US Patent Document 7,288,666
High metathesis activity ruthenium and osmium metal carbene complexes
patent, April 2001
- Grubbs, Robert H.; Schwab, Peter; Nguyen, SonBinh T.
- US Patent Document 6,211,391
Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis
patent, October 2003
- Herrmann, Wolfgang Anton; Schattenmann, Wolfgang; Weskamp, Thomas
- US Patent Document 6,635,768
Latent Photoactivatable Precatalysts for Metathesis Polymerization
patent-application, January 2011
- Buchmeiser, Michel R.; Wang, Dongren
- US Patent Application 12/866806; 20110003905
Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts
patent, November 2004
- Grubbs, Robert H.; Sanford, Melanie S.; Moore, Jason L.
- US Patent Document 6,818,586
Acid-etch resistant, protective coatings
patent, July 2014
- Tang, Tingji; Xu, Gu; Zhong, Xing-Fu
- US Patent Document 8,771,927
Photoresist monomers, polymers thereof and photoresist compositions containing it
patent, February 2003
- Choi, Jae-Hak; Kim, Myoung Soo
- US Patent Document 6,514,666
Metathesis of Electron-Rich Olefins:Â Structure and Reactivity of Electron-Rich Carbene Complexes
journal, May 2002
- Louie, Janis; Grubbs, Robert H.
- Organometallics, Vol. 21, Issue 11
Rapid self-assembly of block copolymers to photonic crystals
patent-application, December 2013
- Xia, Yan; Sveinbjornsson, Benjamin R.; Grubbs, Robert H.
- US Patent Application 13/800646; 20130324666
High metathesis activity ruthenium and osmium metal carbene complexes
patent, February 2003
- Grubbs, Robert H.; Schwab, Peter; Nguyen, SonBinh T.
- US Patent Document 6,515,084
Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
patent, May 1994
- Grubbs, Robert H.; Johnson, Lynda Kaye; Nguyen, SonBinh T.
- US Patent Document 5,312,940
Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water
patent, November 2002
- Lynn, David M.; Dias, Eric L.; Grubbs, Robert H.
- US Patent Document 6,486,279
Homobimetallic and heterobimetallic alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands
patent, September 2004
- Herrmann, Wolfgang Anton; Kohl, Florian J.; Weskamp, Thomas
- US Patent Document 6,787,620
Polymerizable and Polymerized Compositions Comprising and Unsaturated Guanamine and Acrylonitrile
patent, December 1955
- Padbury, John J.; Price, John A.
- US Patent Document 2,726,229
Metathesis of Nitrile Rubbers In the Presence of Transition Metal Complex Catalysts
patent-application, February 2009
- Ong, Christopher; Obrecht, Werner; Nuyken, Oskar
- US Patent Application 12/190840; 20090054597
Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water
patent-application, May 2002
- Lynn, David M.; Dias, Eric L.; Grubbs, Robert H.
- US Patent Application 09/882776; 20020055598
Catalyst Compositions and Their Use for Hydrogenation of Nitrile Rubber
patent-application, June 2015
- Liu, Qingchun; Wei, Zhenli
- US Patent Application 14/348912; 20150166686
3-D interconnected multi-layer microstructure of thermoplastic materials
patent, July 2009
- Ryu, WonHyoung; Bai, Seoung Jai; Hammerick, Kyle
- US Patent Document 7,557,051
High metathesis activity ruthenium and osmium metal carbene complexes
patent-application, September 2003
- Grubbs, Robert H.; Schwab, Peter; Nguyen, Sonbinh T.
- US Patent Application 10/325998; 20030181609
Hexacoordinated ruthenium or osmium carbene catalysts
patent, June 2000
- Van Der Schaaf, Paul Adriaan; Hafner, Andreas; Muhlebach, Andreas
- US Patent Document 6,077,805
Synthesis of ruthenium or osmium metathesis catalysts
patent, November 2000
- Grubbs, Robert H.; Belderrain, Tomas R.; Brown, Seth N.
- US Patent Document 6,153,778
Photogeneration of a Phosphonium Alkylidene Olefin Metathesis Catalyst
journal, July 2012
- Khalimon, Andrey Y.; Leitao, Erin M.; Piers, Warren E.
- Organometallics, Vol. 31, Issue 15
Ruthenium metal alkylidene complexes coordinated with triazolylidene ligands that exhibit high olefin metathesis activity
patent, July 2002
- Grubbs, Robert H.; Trinka, Tina M.
- US Patent Document 6,426,419
Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts
patent-application, November 2002
- Grubbs, Robert H.; Love, Jennifer A.; Sanford, Melanie S.
- US Patent Application 10/017489; 20020177710
Frequency doubling hybrid photoresist having negative and positive tone components and method of preparing the same
patent, September 2000
- Hakey, Mark C.; Holmes, Steven J.; Horak, David V.
- US Patent Document 6,114,082
Organic Electroluminescent Materials and Devices
patent-application, September 2015
- Szigethy, Geza; Murray, Christopher B.; Brooks, Jason
- US Patent Application 14/194245; 20150249222
Light-induced olefin metathesis
journal, January 2010
- Vidavsky, Yuval; Lemcoff, N. Gabriel
- Beilstein Journal of Organic Chemistry, Vol. 6
Cationic RuII Complexes with N-Heterocyclic Carbene Ligands for UV-Induced Ring-Opening Metathesis Polymerization
journal, April 2008
- Wang, Dongren; Wurst, Klaus; Knolle, Wolfgang
- Angewandte Chemie International Edition, Vol. 47, Issue 17
Photoresist Composition
patent-application, October 2012
- Robinson, Alex; Palmer, Richard; Preece, Jon Andrew
- US Patent Application 13/505601; 20120251953
Olefin metathesis coupling using ruthenium and osmium carbene complexes
patent, May 1998
- Grubbs, Robert H.; Nguyen, SonBinh T.
- US Patent Document 5,750,815
Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts
patent-application, April 2003
- Grubbs, Robert H.; Sanford, Melanie S.; Moore, Jason L.
- US Patent Application 10/172765; 20030069374
Methods for Preparing Ruthenium Carbene Complex Precursors and Ruthenium Carbene Complexes
patent-application, April 2013
- Kunz, Linda A.; Cohen, Steven A.
- US Patent Application 13/606640; 20130096314
High metathesis activity ruthenium and osmium metal carbene complexes
patent, August 2000
- Grubbs, Robert H.; Schwab, Peter; Nguyen, SonBinh T.
- US Patent Document 6,111,121
Ring-opening hydrogenated copolymer and process for producing the same
patent, March 1993
- Nishi, Yoshikatsu; Oshima, Masayoshi; Kohara, Teiji
- US Patent Document 5,191,026
High metathesis activity ruthenium and osmium metal carbene complexes
patent-application, October 2006
- Grubbs, Robert H.; Schwab, Peter; Nguyen, Sonbinh T.
- US Patent Application 11/472137; 20060241317
Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
patent, August 1994
- Grubbs, Robert H.; Johnson, Lynda Kaye; Nguyen, SonBinh T.
- US Patent Document 5,342,909
Chemically Amplified Positive Resist Composition and Pattern Forming Process
patent-application, May 2013
- Yasuda, Hiroyuki; Takemura, Katsuya; Tagami, Shohei
- US Patent Application 13/678868; 20130129988
Rapid self-assembly of brush block copolymers to photonic crystals
journal, August 2012
- Sveinbjornsson, B. R.; Weitekamp, R. A.; Miyake, G. M.
- Proceedings of the National Academy of Sciences, Vol. 109, Issue 36, p. 14332-14336
Photolithographic Olefin Metathesis Polymerization
journal, October 2013
- Weitekamp, Raymond A.; Atwater, Harry A.; Grubbs, Robert H.
- Journal of the American Chemical Society, Vol. 135, Issue 45
Process for preparing acyclic olefins using homobimetallic and heterobimetallic alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands
patent, April 2003
- Herrmann, Wolfgang Anton; Kohl, Florian J.; Weskamp, Thomas
- US Patent Document 6,552,139
"Low ""K"" factor hybrid photoresist"
patent, February 2001
- Holmes, Steve; Katnani, Ahmad D.; Patel, Niranjan M.
- US Patent Document 6,190,829
Periodic Nanostructures From Self Assembled Wedge-Type Block-Copolymers
patent-application, November 2013
- Xia, Yan; Sveinbjornsson, Benjamin R.; Grubbs, Robert H.
- US Patent Application 13/801710; 20130296491
Synthesis of ruthenium or osmium metathesis catalysts
patent, June 1999
- Grubbs, Robert H.; Belderrain, Tomas R.; Brown, Seth N.
- US Patent Document 5,917,071
High Metathesis Activity Ruthenium and Osmium Metal Carbene Complexes
patent-application, January 2009
- Grubbs, Robert H.; Schwab, Peter; Nguyen, Sonbinh T.
- US Patent Application 11/929358; 20090012248
Novel ruthenium metal alkylidene complexes coordinated with triazolylidene ligands that exhibit high olefin metathesis activity
patent-application, January 2002
- Grubbs, Robert H.; Trnka, Tina M.
- US Patent Application 09/770993; 20020013473
Synthesis of ruthenium or osmium metathesis catalysts
patent, November 2001
- Grubbs, Robert H.; Belderrain, Tomas R.; Brown, Seth N.
- US Patent Document 6,313,332
Schiff base derivatives of ruthenium and osmium olefin metathesis catalysts
patent, November 1999
- Grubbs, Robert H.; Chang, Sukbok; Jones, Leroy
- US Patent Document 5,977,393
High metathesis activity ruthenium and osmium metal carbene complexes
patent, November 1998
- Grubbs, Robert H.; Schwab, Peter; Nguyen, SonBinh T.
- US Patent Document 5,831,108
Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water
patent, September 2001
- Lynn, David M.; Dias, Eric L.; Grubbs, Robert H.
- US Patent Document 6,284,852
Methanofullerenes
patent-application, September 2014
- Robinson, Alex Philip Graham; Preece, Jon Andrew; Palmer, Richard Edward
- US Patent Application 14/187649; 20140255849
Synthesis of Isocyanate-Based Brush Block Copolymers and Their Rapid Self-Assembly to Infrared-Reflecting Photonic Crystals
journal, August 2012
- Miyake, Garret M.; Weitekamp, Raymond A.; Piunova, Victoria A.
- Journal of the American Chemical Society, Vol. 134, Issue 34
Process for the Preparation of Hydrogenated Nitrile Rubber
patent-application, December 2012
- Ong, Christopher; Mueller, Julias Maria
- US Patent Application 13/391633; 20120329954
Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis
patent, November 2007
- Herrmann, Wolfgang Anton; Schattenmann, Wolfgang; Weskamp, Thomas
- US Patent Document 7,294,717
Direct Photopatterning of Robust and Diverse Materials
patent-application, April 2015
- Weitekamp, Raymond; Grubbs, Robert H.; Atwater, Harry A.
- US Patent Application 14/505824; 20150118188
High metathesis activity ruthenium and osmium metal carbene complexes
patent-application, May 2005
- Grubbs, Robert H.; Schwab, Peter; Nguyen, Sonbinh T.
- US Patent Application 10/968361; 20050113590
High metathesis activity ruthenium and osmium metal carbene complexes
patent, September 2006
- Grubbs, Robert H.; Schwab, Peter; Nguyen, SonBinh T.
- US Patent Document 7,102,047
Photonic structures from self assembly of brush block copolymers and polymer blends
patent-application, January 2014
- Miyake, Garret M.; Weitekamp, Raymond; Grubbs, Robert H.
- US Patent Application 13/930400; 20140011958